luxury properties for rent Madison, United States

Welcome to your ultimate winter retreat! Available for rent for the very first time, this meticulously remodeled 3-bedroom Colonial offers an unparalleled blend of modern luxury, cozy comfort, and complete privacy. Every inch of this home has been thoughtfully designed and comes fully furnished with exceptional, high-end decor throughout. Step inside to find a bright and spacious family room featuring a generous dining area-the absolute perfect setup for hosting holiday dinners and warm family gatherings. The flexible floor plan is designed for convenience, offering comfortable first-floor bedrooms and an additional private bedroom suite on the second level. Outside, embrace the beauty of the season on your private side deck, complete with a cozy gas fire pit. Whether you're sipping morning coffee or stargazing on a crisp winter night, this space is designed for all-season enjoyment. Situated on 6.5 acres of serene, wooded land, you will enjoy ultimate peace and privacy while still being close to local winter attractions. This is not your average rental-it is a pristine, loved home waiting to host your perfect winter season. Just bring your toothbrush and move right in!

Where New England architecture meets timeless elegance! Experience the pinnacle of shoreline living in this spectacular waterfront estate, perfectly positioned on a private, peninsula-like setting in Sachem's Head community. Boasting breathtaking, panoramic views of Long Island Sound, this 1930s residence is a masterwork of historic character and unique architectural artistry. The home's rich heritage is reflected in its exquisite details, from the enduring beauty of Stony Creek Granite and warm Pecky Cypress woodwork, to the original porthole windows in the grand family room. In the formal dining room, a distinctive ribbed ceiling, designed to evoke the overhead of a classic ship's cabin, creates an unforgettable atmosphere for entertaining. The heart of the home features a generous galley kitchen that balances functionality with style, offering abundant cabinetry, expansive counter space, and dining area with plenty of windows making sure no view is missed. Retreat to the second floor to find six spacious bedrooms, each offering its own unique perspective of the water, while the finished third-floor flex space serves as an ideal game room or private sanctuary. Spread across two manicured acres, enjoy relaxed seaside living with multiple sun porches and expansive patio for gatherings. Take advantage of the Vineyard Place Association amenities, all while being just a short drive from charming downtown Guilford!

The views from this charming Sachems Head waterfront home are exceptional. Located next to the Sachems Head Yacht Club this fully furnished academic rental is a dream come true. Four bedrooms and two full baths, with an additional bedroom and full bath on the ground level in the warmer months. Additional rooms offer an excellent option for home offices. The main level features a wood-burning fireplace and an open floor plan with views from nearly every window. Available September 1, 2026 through June 1, 2027. Flexibility in early June extension. Pets are considered with owner approval. Excellent credit required. Showings by appointment only.

Welcome to 14 Island View Ave-a masterfully redesigned coastal retreat nestled in the heart of highly desirable Pine Orchard. Spanning 2,100 square feet, this thoughtfully renovated home seamlessly blends modern luxury with relaxed shoreline living. Boasting 5 spacious bedrooms and 2.5 beautifully appointed baths, the residence features a bright, open floor plan optimized to capture gorgeous, unobstructed water views. Every detail has been meticulously curated during its full remodel, offering an unparalleled turn-key experience in one of the area's most coveted neighborhoods.

Step into this delightful and charming fisherman's cottage in the heart of downtown Old Saybrook. Built in 1800, 43 Pennywise Lane blends warm and cozy character with surprising spaciousness. The owner has preserved this home's historical integrity while adding in modern comforts. The first floor features an oversized primary suite with full bath, office space and reading nook. The eat-in kitchen is highlighted by gleaming wood counters and a beautiful decorative fireplace. Rounding out the first floor, you'll find the sun filled napping corner, a tucked away charming TV area and a second full bath. You'll also appreciate the mini-mudroom drop zone perfect for your bags, boots and hats! Upstairs you'll find an additional bedroom and a second media or lounge area. This space is ideal for guests or a quiet place to unwind. Enjoy the convenience of an outdoor shower, grill, fire pit and the nicely sized, partially fenced in yard. Fancy a stroll to town? It's just down the block with terrific shopping and dining. Enjoy all the amenities that make this shoreline town so popular and accessible, including access to Amtrak and the Shoreline East Train. Tenant: renters insurance, heat, electric, water and a one time end of lease cleaning. Landlord: all other utilities. No pets or smoking. A truly special place to hang your hat. July and August 2026. Also available September 15, 2026 - May 31, 2027 for 3K per month.

Live the Good Life in Historic Essex Village! This beautifully renovated 3 level apartment in an 1880 duplex home blends timeless charm with modern design in the heart of the Connecticut River Valley. Thoughtfully reimagined with an architecturally designed open floor plan, the light-filled first floor features soaring 9+ foot ceilings and generous spaces for living, dining, and entertaining. The stylish kitchen boasts stainless steel appliances, granite countertops, and crisp white cabinetry. A full bath completes the main level. Upstairs, the private primary suite offers a serene retreat with its own full bath, dressing area, and a wall of closets. The third floor provides flexible space-ideal for a home office or storage. Comfort is ensured with split-unit AC/heat on all levels and efficient oil-fired hot water heat on the first and second floors. Laundry is conveniently located in the basement. Relax on your private backyard patio. Just steps from your front door, enjoy Essex's unique shops, fine dining, scenic marinas, and the beautiful Connecticut River. Perfectly situated midway between New York and Boston, this is Village living at its very best!

Rarely available! This historic 1860 Essex Village waterfront home is nestled on a quiet lane with direct waterfront on Middle Cove. Step back in time and experience the charm of this Vintage home, complete with many original features, while still enjoying modern amenities and updated appliances. The home boasts original wood floors, a stunning floor-to-ceiling bay window in the living room, and a built-in hutch with a Butler's Pantry in the dining room. Upstairs, the primary bedroom is a spacious two-room suite, accompanied by an additional bedroom and bath. The semi-finished lower level, reminiscent of a cozy tavern room, provides walkout access to the patio, backyard, and waterfront. View stunning sunsets over Middle Cove! Relax on the inviting front porch or take a short stroll to the Griswold Inn, Noah's, the Black Seal, and an array of charming shops, yacht clubs, and marinas. The barn outbuilding is not included in the rental. No pets, no smoking. Minimum 1-year lease. Conveniently located halfway between New York and Boston. You will love living in one of the Historic Homes of Essex Village!

A Timeless Summer Tradition: Renovated Victorian Shingled beach house in the Borough of Fenwick Experience the quintessential New England summer in the historic Borough of Fenwick. This stunning, shingle-style Victorian beach house seamlessly blends old-world coastal charm with modern, high-end luxury. Featuring 8 spacious bedrooms and 4.5 baths, this expansive residence is the perfect sanctuary for large families or those who love to entertain against the backdrop of the Long Island Sound. The heart of the home is a totally renovated gourmet eat-in kitchen, designed for the culinary enthusiast and large-scale hosting. Beyond the kitchen, life slows down on the magnificent wrap-around screened porch-the perfect vantage point to enjoy your morning coffee or an evening cocktail while overlooking the water and catching the sea breeze. Retreat to the third floor, where a dedicated playroom offers a private escape or a quiet workspace away from the main living areas. From its cedar-shingled exterior to its thoughtfully updated interior, every inch of this home invites you to relax, recharge, and rediscover the magic of a Fenwick summer.

Beautifully renovated and furnished home with direct water views!! Located directly across from the Pardee Seawall Park on the Long Island Sound, don't miss this 2 bedroom colonial cottage that has it all. New hardwood floors in the living room and bedrooms, along with beautiful tiles in both bathrooms and kitchen. Kitchen fully renovated with quartz counter tops and brand new stainless steel appliances. Laundry room right off of the kitchen with a new stackable washer and dryer unit. Detached garage and plenty of off street parking spaces. Cathedral ceilings in the master bedroom with direct water views off a large balcony. Close to many restaurants, shopping, parks, and I-95. Available August 31st to May.

Academic furnished rental in White Sands Beach. Large living room with fireplace, dining room with table for eight, fully applianced kitchen, sunroom/office, laundry and full bath all on the first floor.The four bedrooms and newly updated hall bath are upstairs. Cable and wi-fi installed. Across the road are a tot lot, basketball court and large open space for other games. A short walk to the Association beach. New hardwood floors installed upstairs . Rental start date is September 1.

Discover this charming, free-standing cottage, perfectly situated behind a quiet, 4-unit multifamily colonial. This inviting 2-bedroom, 1-bath home features a spacious living area and an eat-in kitchen. Residents will enjoy a shared driveway and laundry in a peaceful East Rock location-just minutes from Yale University, hospitals, local bus lines, dining, and shops. The landlord is seeking long-term tenants. Please note: no pets or smoking permitted. A credit score of 670 or better is required, and applicants should submit credit reports and references via RentSpree.

Rental Available August 25, 2026- June 15, 2027 An incredible East Rock opportunity. This magnificent 5 BR furnished home is available for academic rent. An elevator takes you to all 3 floors of this amazing home as well as down to the full dry basement perfect for storage. Main floor boasts a Living room, dining room, a huge kitchen that opens to a family room as well as a big deck that leads to a fully fenced in private yard. The second floor has 4 BR's, one with built-ins doubles as a great home office.2 full beautiful new baths. The third floor is fabulous! A private family room, loft, huge bonus room, a bedroom and new beautiful bathroom. Tons of built in bookshelves throughout. Gas heat, central air. Located in the private corner of Everit street across from the park with off street parking. Minutes to Foote school and a short walk to Yale and Downtown New Haven. No smoking. No pets. 700 Minimum credit score. LISTING AGENT MUST BE AT ALL SHOWINGS AND TIMES ARE LIMITED SO PLEASE GIVE PLENTY OF NOTICE Rentspree Application Accepted

Offered Sept $8,000. Enjoy the ease of summer on the North Fork in this classic 1910 hilltop home overlooking Orient Bay and Long Island Sound. A three-sided wraparound porch extends the main living spaces outdoors through multiple glass doors, creating a seamless indoor-outdoor flow filled with light and salt breezes. Inside, the home offers inviting spaces for gathering, including a spacious living room with a wood-burning fireplace, a formal dining room, and a generous eat-in kitchen with a butler’s pantry. A TV room/bedroom and full bath complete the ground floor. Upstairs are five bedrooms, including a primary bedroom with a private balcony and half bath, along with a full bath for the four additional bedrooms. The private grounds include an in-ground pool. Latham’s Farm Stand and Orient Village are just a short walk away. September is an ideal time to enjoy this peaceful, timeless retreat.

Authentic 1770 Cottage in the heart of Orient Village. Lovingly restored & maintained Village home on beautifully landscaped lot, offering private grounds & distant views of sunsets over the bay. Furnished in period antiques, screened-in porch off kitchen, first floor bedroom. Walk to amenities, bay beach, Yacht Club, marina, farm stand & Jitney. Offered Sept 3-Oct 3 for $8,000. Permit #0091.

Beautiful renovated 2-bedroom, 2 full bath home in Orient Village. Open concept – living/dining/gourmet kitchen. Lower level with screening room, office, full bath. Walk from Jitney. Enjoy all village amenities, bay & sound beaches. Close to Orient Beach State Park & Cross Sound Ferry. Available April $5,000; May $5,000; June $7,000; July $15,000; Aug $15,000; Sept $8,000. Permit# 1364.